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Research Articles

Quantum Chemical Investigations on the Hydrogen-Bonded Interactions of Bioactive Molecule N2-(4-Methoxysalicylidene) Arginine Hemihydrate

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Pages 7651-7672 | Received 02 Jun 2022, Accepted 17 Oct 2022, Published online: 03 Nov 2022

References

  • J. Lewis, M. Matteucci, T. Chen, and H. Jiao, “Hypoxia Activated Drugs of Nitrogen Mustard Alkylators as Anticancer Agents and Their Preparation” (WO Patent 2009140553 A2, 2009).
  • J.C. Moutet, and A. Ourari, “Electrocatalyticepoxidation and Oxidation with Dioxygen Using Manganese (III) Schiff-Base Complexes,” Electrochimica Acta 42, no. 16 (1997): 2525–31.
  • K. Srinivasan, P. Michaud, and J.K. Kochi, “Epoxidation of Olefins with Cationic (Salen) Manganese (III) Complexes. The Modulation of Catalytic Activity by Substituents,” Journal of the American Chemical Society 108, no. 9 (1986): 2309–20.
  • A.v. Konig, F. Moll, and L. Rosenhahn, “Photographic Material, Process for the Production Thereof and Process for the Production of Photographic Images” (US Patent 4358531, 1982).
  • N. Elangovan, R. Thomas, and S. Sowrirajan, “Synthesis of Schiff Base (E)-4-((2-Hydroxy-3,5- Diiodobenzylidene)Amino)-N-Thiazole-2-yl)Benzenesulfonamide with Antimicrobial Potential, Structural Features, Experimental Biological Screening and Quantum Mechanical Studies,” Journal of Molecular Structure 1250 (2022): 131762.
  • M.M. Abd-Elzaher, A.A. Labib, H.A. Mousa, S.A. Moustafa, M.M. Ali, and A.A. El- Rashedy, “Synthesis, Anticancer Activity and Molecular Docking Study of Schiff Base Complexes Containing Thiazole Moiety,” Beni-Suef University Journal of Basic and Applied Sciences 5, no. 1 (2016): 85–96.
  • M. Krátký, M. Dzurková, J. Janoušek, K. Kone ˇcná, F. Trejtnar, J. Stolaˇríková, and J. Vinšová, “Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis,” Antimicrobial Activity and Cytotoxicity, Molecules (2017): 22.
  • W. Hu, W. Zhou, C. Xia, and X. Wen, “Synthesis and Anticancer Activity of Thiosemicarbazones,” Bioorganic & Medicinal Chemistry Letters 16, no. 8 (2006): 2213–8.
  • D.F. Smee and R.W. Sidwell, “Viruses of the Bunya-and Togaviridae Families: potential as Bioterrorism Agents and Means of Control,” Antiviral Research 57, no. 1–2 (2003): 41–52.
  • L. Li, I. Vorobyov, and T.W. Allen, “The Different Interactions of Lysine and Arginine Side Chains with Lipid Membranes,” The Journal of Physical Chemistry-B 117, no. 40 (2013): 11906–20.
  • E. Nemoto, H. Takahashi, D. Kobayashi, H. Ueda, and Y. Morimoto, “Effects of poly-L-Arginine on the Permeation of Hydrophilic Compounds through Surface Ocular Tissues,” Biological & Pharmaceutical Bulletin 29, no. 1 (2006): 155–60.
  • I. Westergren and B.B. Johansson, “Altering the Blood-Brain Barrier in the Rat by Intracarotid Infusion of Polycations: A Comparison between Protamine, Poly-L-Lysine and poly-L-Arginine,” Acta Physiologica Scandinavica 149, no. 1 (1993): 99–104.
  • L. Vidal, V. Thuault, A. Mangas, R. Coveñas, A. Thienpont, and M. Geffard, “Lauryl-poly-L-Lysine: A New Antimicrobial Agent?,” Journal of Amino Acids 2014 (2014): 672367.
  • M. Nishikawa and K.I. Ogawa, “Antimicrobial Activity of a Chelatable Poly (Arginyl-Histidine) Produced by the Ergot Fungus Verticillium Kibiense,” Antimicrobial Agents and Chemotherapy 48, no. 1 (2004): 229–35.
  • Q. Lan, Y. Wang, S. Wang, and Y. Liu, “In Vitro Study of Alginate/poly-L-Arginine Microcapsules as a Protein or Anticancer Drug Carrier,” IFMBE Proceedings 19 (2008): 32–5.
  • F. Mattner, J.K. Fleitmann, K. Lingnau, W. Schmidt, A. Egyed, and J. Fritz, “Vaccination with Poly-l-Arginine as Immuno Stimulant for Peptide Vaccines: Induction of Potent and Long-Lasting T-Cell Responses against Cancer Antigens,” Cancer Res 62 (2002): 1477–80.
  • S. Plianwong, P. Opanasopit, T. Ngawhirunpat, and T. Rojanarata, “Chitosan ‘Combined with poly-L-Arginine as Efficient, Safe, and Serum-Insensitive Vehicle with RNase Protection Ability for siRNA Delivery,” BioMed Research International 2013 (2013): 574136.
  • B.P. Meloni, L.M. Brookes, V.W. Clark, J.L. Cross, A.B. Edwards, R.S. Anderton, R.M. Hopkins, K.Hoffmann, and N.W. Knuckey, “Poly-Arginine and Arginine-Rich Peptides Are Neuro Protective in Stroke Models,” Journal of Cerebral Blood Flow and Metabolism 35, no. 6 (2015): 993–1004.
  • M. Sethuram, G. Bhargavi, M. Dhandapani, G. Amirthaganesan, and M. NizamMohideen, “N2-(4-Methoxysalicylidene) Arginine Hemihydrate,” Acta Crystallographica-Section E, Structure Reports Online 69, no. Pt 8 (2013): o1301–o1302.
  • M.J. Frisch, G.W. Trucks, H.B. Schkegel, G.C. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Bloino, et al, Gaussian 09, Revision D.01, Gaussian Inc (Wallingford CT, 2013).
  • E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, NBO Version 3.1, TCI, University of Wisconsin, Madison, 1998.
  • T. Sundius, “Scaling of ab Initio Force Fields by MOLVIB,” Vibrational Spectroscopy 29, no. 1-2 (2002): 89–95.
  • T. Sundius, “Molvib – A Flexible Program for Force Field Calculations,” Journal of Molecular Structure 218 (1990): 321–6.
  • P. Pulay, G. Fogarasi, G. Pongor, J.E. Boggs, and A. Vargha, “Combination of Theoretical ab Initio and Experimental Information to Obtain Reliable Harmonic Force Constants. Scaled Quantum Mechanical (QM) Force Fields for Glyoxal, Acrolein, Butadiene, Formaldehyde, and Ethylene,” Journal of the American Chemical Society 105, no. 24 (1983): 7037–47.
  • R. Dennington, T.A. Keith, and J.M. Millam, Gauss View, Version 6.1 (Shawnee Mission, KS: Semi chem Inc., 2016).
  • S.K. Wolff, D.J. Grimwood, J.J. McKinnon, M.J. Turner, D. Jayatilaka, and M.A. Spackman, Crystal Explorer (Version 2.2) (Crawley, Australia: University of Western Australia, 2010).
  • T. Lu and F. Chen, “Multiwfn: A Multifunctional Wavefunction Analyser,” Journal of Computational Chemistry 33, no. 5 (2012): 580–92.
  • W. Humphrey, A. Dalke, and K. Schulten, “VMD: Visual Molecular Dynamics,” Journal of Molecular Graphics 14, no. 1 (1996): 33–8.
  • G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson, “Autodock4 and AutoDockTools4: automated Docking with Selective Receptor Flexiblity,” Journal of Computational Chemistry 30, no. 16 (2009): 2785–91.
  • G. Keresztury, S. Holly, G. Besenyei, J. Varga, A.Y. Wang, and J.R. Durig, “Vibrational Spectra of monothiocarbamates-II. IR and Raman Spectra, Vibrational Assignment, Conformational Analysis and ab Initio Calculations of S-methyl-N,N-Dimethylthiocarbamate,” Spectrochimica Acta. 49, no. 13–14 (1993): 2007–26.
  • G. Keresztury, in Raman Spectroscopy: Theory in Handbook of Vibrational Spectroscopy, edited by J.M. Chalmers, P.R. Griffith, vol. 1 (New York: John Wiley & Sons Ltd., 2002).
  • K.J. Cutrona, B.A. Kaufman, D.M. Figueroa, and D.E. Elmore, “Role of Arginine and Lysine in the Antimicrobial Mechanism of Histone-Derived Antimicrobial Peptides,” FEBS Letters 589, no. 24 Pt B (2015): 3915–20.
  • T.J. Beaula, P. Muthuraja, M. Dhandapani, and V. Bena Jothy, “Effect of Charge Transfer with Spectral Analysis on the Antibacterial Compound 4-(Dimethylamino) Pyridine: 3,5-Dinitrobenzoic Acid: Experimental and Theoretical Perspective,” Journal of Molecular Structure 1171 (2018): 511–26.
  • L. Padmaja, C. Ravikumar, D. Sajan, I. Hubert Joe, V.S. Jayakumar, G.R. Pettit, and O. Faurskov Nielsen, “Density Functional Study on the Structural Conformations and Intramolecular Charge Transfer from the Vibrational Spectra of the Anticancer Drug combretastatin-A2,” Journal of Raman Spectroscopy 40, no. 4 (2009): 419–28.
  • “Computational Chemistry Comparison and Benchmark Data Base Release 21,” NIST Stand. Ref. Database 101 (2020).
  • J.P. Merrick, D. Moran, and L. Radom, “An Evaluation of Harmonic Vibrational Frequency Scale Factors,” The Journal of Physical Chemistry. A 111, no. 45 (2007): 11683–700.
  • F.R. Dollish, W.G. Fateley, and F.F. Bentley, Characteristic Raman Frequencies of Organic Compounds (New York: Wiley, 1973).
  • X.D. Divya Dexlin, J.D. Deephlin Tarika, M. Sethuram, and T. Joselin Beaula, “Synthesis, Vibrational Depictions, IRI Interpretations and Docking Research on Coordination Metal Complex Diaqua Aspartato Zinc (II) Monohydrate Using DFT Approach,” Journal of Molecular Liquids 351 (2022): 118687.
  • J. Binoy, C. James, I. Hubert Joe, and V.S. Jayakumar, “Vibrational Analysis and Y-Aromaticity in Bis (N,N′-Diphenylguanidinium) Oxalate Crystal: A DFT Study,” Journal of Molecular Structure 784, no. 1–3 (2006): 32–46.
  • C. James, V.S. Jayakumar, and I. Hubert Joe, “Natural Bond Orbital Analysis and Vibrational Spectroscopic Studies of H-Bonded N,N′-Diphenylguanidinium Nitrate,” Journal of Molecular Structure 830, no. 1–3 (2007): 156–66.
  • V. Sasikala, D. Sajan, K. Job Sabu, T. Arumanayagam, and P. Murugakoothan, “Electronic Structure, Vibrational Spectral and Intervening Orbital Interactions Studies of NLO Material: Guanidinium 4-Nitrobenzoate,” Spectrochimica Acta-Part A, Molecular and Biomolecular Spectroscopy 139 (2015): 555–72.
  • T. Joselin Beaula, A. Packiavathi, D. Manimaran, I. Hubert Joe, V.K. Rastogi, and V. Bena Jothy, “Quantum Chemical Computations, Vibrational Spectroscopic Analysis and Antimicrobial Studies of 2,3-Pyrazinedicarboxylic Acid,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 138 (2015): 723–35.
  • G. Varsanyi, Vibrational Spectra of Benzene Derivative (New York: Academic Press, 1969).
  • M.S. Weiss, M. Brandl, J. Sühnel, D. Pal, and R. Hilgenfeld, “More Hydrogen Bonds for the (Structural) Biologist,” Trends in Biochemical Sciences 26, no. 9 (2001): 521–3.
  • M. Gümüş, Ş.N. Babacan, Y. Demir, Y. Sert, İ. Koca, and İ. Gülçin, “Discovery of Sulfadrug-Pyrrole Conjugates as Carbonic Anhydrase and Acetylcholinesterase Inhibitors,” Archiv Der Pharmazie 355, no. 1 (2022): 2100242.
  • N.P.G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures (New York: Wiley, 1994).
  • S. Gunasekaran, S.R. Varadhan, and K. Manoharan, “Fourier Transform Infrared and Laser Raman Spectroscopic Investigations on 2-N- (Benzoylamino) Pyridine,” Indian J. Phys 67B, no. 1 1993): 95–101.
  • C.S. Hiremath, J. Yenagi, and J. Tonannavar, “FT-Raman and Infrared Spectra and Vibrational Assignments for 3-Chloro-4-Methoxybenzaldehyde, as Supported by ab Initio, Hybrid Density Functional Theory and Normal Coordinate Calculations,” Spectrochimica Acta-Part A, Molecular and Biomolecular Spectroscopy 68, no. 3 (2007): 710–7.
  • V. Hernandez, C. Castiglioni, and G. Zerbi, “Hyperconjugation from Infrared Intensities: The Case of Methyl Acetate and of Its Selectively Deuterated Derivatives,” Journal of Molecular Structure 324, no. 1–2 (1994): 189–98.
  • T.K. Kuruvilla, J.C. Prasana, S. Muthu, and J. George, “Vibrational Spectroscopic (FT-IR, FT-Raman) and Quantum Mechanical Study of 4-(2-Chlorophenyl)-2-Ethyl-9-Methyl-6H-Thieno[3,2-f] [1,2,4]Triazolo[4,3- a] [1,4] Diazepine,” Journal of Molecular Structure. 1157 (2018): 519–29.
  • C. Ravikumar, I. Hubert Joe, and D. Sajan, “Vibrational Contributions to the Second-Order Nonlinear Optical Properties of π-Conjugated Structure Acetoacetanilide,” Chemical Physics 369, no. 1 (2010): 1–7.
  • P. Gupta and J.K. Gupta, “Synthesis and in-Vitro Antifungal Evaluation of 5- Pyrazolones,” Open Chemistry Journal 3, no. 1 (2016): 17–24.
  • C. Ravikumar, I. Hubert Joe, and V.S. Jayakumar, “Charge Transfer Interactions and Nonlinear Optical Properties of Push–Pull Chromophorebenzaldehydephenylhydrazone: A Vibrational Approach,” Chemical Physics Letters 460, no. 4–6 (2008): 552–8.
  • G. Treboux, D. Maynau, and J.P. Malrieu, “Combining Molecular Mechanics with Quantum Treatments for Large Conjugated Hydrocarbons. 2. A Geometry-Dependent Heisenberg Hamiltonian,” The Journal of Physical Chemistry 99, no. 17 (1995): 6417–23.
  • M. Silverstein, G.C. Basseler, and C. Morill, Spectrometric Identification of Organic Compounds (New York: Wiley, 1981).
  • V. Krishnakumar, G. Keresztury, T. Sundius, and S. Seshadri, “Density Functional Theory Study of Vibrational Spectra and Assignment of Fundamental Vibrational Modes of 1-Methyl-4-Piperidone,” Spectrochimica Acta-Part A, Molecular and Biomolecular Spectroscopy 68, no. 3 (2007): 845–50.
  • R.K. Singh, A.K. Singh, S. Siddiqui, M. Arshad, and A. Jafri, “Synthesis, Molecular Structure, Spectral Analysis and Cytotoxic Activity of Two New Aroylhydrazones,” Journal of Molecular Structure. 1135 (2017): 82–97.
  • A. Cavalli, X. Salvatella, C.M. Dobson, and M. Vendruscolo, “Protein Structure Determination from NMR Chemical Shifts Proc,” Proceedings of the National Academy of Sciences of the United States of America 104, no. 23 (2007): 9615–20.
  • C.H. Choi and M. Kertesz, “Conformational Information from Vibrational Spectra of Styrene, trans-Stilbene, and cis-Stilbene,” The Journal of Physical Chemistry A 101, no. 20 (1997): 3823–31.
  • Y. Pu, F. Chen, A. Ziebell, B.H. Davison, and A.J. Ragauskas, “NMR Characterization of C3H and HCT down-Regulated Alfalfa Lignin,” BioEnergy Research 2, no. 4 (2009): 198–208.
  • M. Pandey, S. Muthu, and N.M. Nanje Gowda, “Quantum Mechanical and Spectroscopic (FT-IR, FT-Raman,1H,13C NMR, UV-Vis) Studies, NBO, NLO, HOMO, LUMO and Fukui Function Analysis of 5-Methoxy-1H-Benzo[d] Imidazole-2(3H)-Thione by DFT Studies,” Journal of Molecular Structure 1130 (2017): 511–21.
  • M.S. Almutairi, A.S. Zakaria, P.P. Ignasius, R.I. Al-Wabli, I.H. Joe, and M.I. Attia, “Synthesis, Spectroscopic Investigations, DFT Studies, Molecular Docking and Antimicrobial Potential of Certain New Indole-Isatin Molecular Hybrids: Experimental and Theoretical Approaches,” Journal of Molecular Structure 1153 (2018): 333–45.
  • C. Dabora Vincy, J.D. Deephlin Tarika, X.D. Divya Dexlin, A. Rathika, and T. Joselin Beaula, “Exploring the Antibacterial Activity of 1, 2 Diaminoethane Hexanedionic Acid by Spectroscopic, Electronic, ELF, LOL, RDG Analysis and Molecular Docking Studies Using DFT Method,” Journal of Molecular Structure 1247 (2022): 131388.
  • A.A. Abdulridha, M.A. Albo Hay Allah, S.Q. Makki, Y. Sert, H.E. Salman, and A.A. Balakit, “Corrosion Inhibition of Carbon Steel in 1 M H2SO4 Using New Azo Schiff Compound: Electrochemical, Gravimetric, Adsorption, Surface and DFT Studies,” Journal of Molecular Liquids 315 (2020): 113690.
  • R.G. Parr and W. Yang, Functional Theory of Atoms and Molecules (New York: Oxford University Press, 1989).
  • P.W. Ayers and R.G. Parr, “Variational Principles for Describing Chemical Reactions: The Fukui Function and Chemical Hardness Revisited,” Journal of the American Chemical Society 122, no. 9 (2000): 2010–8.
  • B. Silvi and A. Savin, “Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions,” Nature 371, no. 6499 (1994): 683–6.
  • F.R. B, J.C. Prasana, S. Muthu, and C.S. Abraham, “Molecular Docking Studies, Charge Transfer Excitation and Wave Function Analyses (ESP, ELF, LOL) on Valacyclovir: A Potential Antiviral Drug,” Computational Biology and Chemistry 78 (2019): 9–17.
  • Y. Zhang, J. Huang, L. Qiao, X. Zhang, W. Cao, Z. Ding, X. Hang, B. Qin, and J. Song, “Investigations Based on Non-Covalent Interactions in 1-(4-Chloromethylbenzoyl)-3-(4, 6-di-Substituted Pyrimidine-2-yl)Thioureas: Synthesis, Characterizations and Quantum Chemical Calculations,” Journal of Molecular Structure. 1180 (2018): 455–61.
  • J.S. Murray and P. Politzer, “Electrostatic Potentials: chemical Applications,” in Encyclopedia of Computational Chemistry, edited by PvR. Schleyer (West Sussex: Wiley, 1998), 912–20.
  • T. Lu and F. Chen, “Quantitative Analysis of Molecular Surface Based on Improved Marching Tetrahedra Algorithm,” Journal of Molecular Graphics & Modelling 38 (2012a): 314–23.
  • I. Mahmudov, Y. Demir, Y. Sert, Y. Abdullayev, A. Sujayev, S.H. Alwasel, and I. Gulcin, “Synthesis and Inhibition Profiles of N-Benzyl- and N-Allyl Aniline Derivatives against Carbonic Anhydrase and acetylcholinesterase-A Molecular Docking Study,” Arabian Journal of Chemistry 15, no. 3 (2022): 103645.
  • D.A. Filimonov, V.V. Poroikov, E.I. Karaicheva, R.K. Kazaryan, A.P. Boudunova, E.M. Mikhailovsky, A.V. Rudnitskih, L.V. Goncharenko, and Y.V. Burov, “Computer-Aided Prediction of the Biological Activity Spectrum of Chemical Compounds from Their Structural Formulae: PASS Systems,” Experimental and Clinical Psychopharmacology. 58 (1995): 56–62.
  • J.R. Harris, S.A. Balajee, and B.J. Park, “Pneumocystis jirovecii Pneumonia: current Knowledge and Outstanding Public Health Issuesexternal Icon,” Current Fungal Infection Reports 4, no. 4 (2010): 229–37.

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